Sulfur and Azobenzenes, a Profitable Liaison: Straightforward Synthesis of Photoswitchable Thioglycosides with Tunable Properties
Abstract: Azobenzene photoswitches are valuable tools for controlling properties of molecular systems with light. We have been investigating azobenzene glycoconjugates to probe carbohydrate‐protein interactions and to design glycoazobenzene macrocycles with chiroptical and physicochemical properties modulated by light irradiation. To date, direct conjugation of glycosides to azobenzenes was performed by reactions providing target compounds in limited yields. We therefore sought a more effective and reliable coupling method. In this paper, we report on a straightforward thioarylation of azobenzene derivatives with glycosyl thiols as well as other thiols, thereby increasing the scope of azobenzene conjugation. Even challenging unsymmetrical conjugates can be achieved in good yields via sequential or one‐pot procedures. Importantly, red‐shifted azoswitches, which are addressed with visible light, were easily functionalized. Additionally, by oxidation of the sulfide bridge to the respective sulfones, both the photochromic and the thermal relaxation properties of the core azobenzene can be tuned. Utilizing this option, we realized orthogonal three‐state photoswitching in mixtures containing two distinct azobenzene thioglycosides.
- Location
-
Deutsche Nationalbibliothek Frankfurt am Main
- Extent
-
Online-Ressource
- Language
-
Englisch
- Bibliographic citation
-
Sulfur and Azobenzenes, a Profitable Liaison: Straightforward Synthesis of Photoswitchable Thioglycosides with Tunable Properties ; day:01 ; month:06 ; year:2022 ; extent:1
Chemistry - a European journal ; (01.06.2022) (gesamt 1)
- Creator
- DOI
-
10.1002/chem.202200354
- URN
-
urn:nbn:de:101:1-2022060215273592961897
- Rights
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
-
15.08.2025, 7:23 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Berry, Jonathan
- Lindhorst, Thisbe K.
- Despras, Guillaume
Other Objects (12)
Sulfur and Azobenzenes, a Profitable Liaison: Straightforward Synthesis of Photoswitchable Thioglycosides with Tunable Properties
Straightforward, Vol. 2
Straightforward Allocation Mechanisms
Straightforward, Vol. 1
Profitabel.
Xe⋯OCS: Relatively straightforward?
Liaison
Profitable cannibalization
Straightforward : in 2 vol., 1
Straightforward : in 2 vol., 2
"Johannistag" "Entschuldigung" "Profitabel"
Profitable horizontal mergers
Sulfur and Azobenzenes, a Profitable Liaison: Straightforward Synthesis of Photoswitchable Thioglycosides with Tunable Properties
Straightforward, Vol. 2
Straightforward Allocation Mechanisms
Straightforward, Vol. 1
Profitabel.
Xe⋯OCS: Relatively straightforward?
Liaison
Profitable cannibalization
Straightforward : in 2 vol., 1
Straightforward : in 2 vol., 2
"Johannistag" "Entschuldigung" "Profitabel"
Profitable horizontal mergers
Sulfur and Azobenzenes, a Profitable Liaison: Straightforward Synthesis of Photoswitchable Thioglycosides with Tunable Properties
Straightforward, Vol. 2
Straightforward Allocation Mechanisms
Straightforward, Vol. 1
Profitabel.
Xe⋯OCS: Relatively straightforward?
Liaison
Profitable cannibalization
Straightforward : in 2 vol., 1
Straightforward : in 2 vol., 2
"Johannistag" "Entschuldigung" "Profitabel"